Top Reflections of the Decade

by | Dec 30, 2019 | thoughts, life | 2 comments

The last few days of December has always been a time I genuinely look forward to. After all of the holiday festivities and quality time with family and friends, I typically find myself back at home, able to pause and reflect on the last year.

It’s so important to set time aside to reflect and acknowledge how far we’ve come and what lessons we’ve learned. This way, we can go into the upcoming year with more of a “blank slate” mindset and set realistic goals for ourselves of what we hope to accomplish.

As I look back on this last year in particular, I’m filled with quite a few different emotions. Overall, it was a very happy year, full of travels (Italy, Denver, Wilmington, Charleston and Arizona), many family gatherings (especially over the holidays), outings with friends, and a critical year of professional growth at Salesforce and with Lipstick & Ink. But on the flip side, there was also tragic losses of a friend and family friend, family illnesses that came about and tough lessons I had to learn. Similarly to 2018, it was a year of growth for me that I believe is ultimately setting me up for a flourishing 2020.

When I thought about writing this post, I thought about recapping the past year (like I have in the past), but decided that I wanted to instead focus on this last decade. With the 2010’s coming to a close, I’m looking back on everything that happened this last decade and recapping some of my favorite memories, lessons learned, and the areas of my life where I challenged and pushed myself to grow. Check them out below!

Kelly sits on her balcony and writes in her notebook.

If I had to describe the decade in 3 words, they would be:

Pivotal, transformative & eye-opening.

One thing from the decade that I’m most proud of personally or professionally:

I think in general, I’m proud that I have always thought ahead and pushed myself to go after what I want, even when I know I’ll be scared or uncomfortable. One of those instances was undoubtedly launching Lipstick & Ink. I was nervous about showing vulnerability and putting myself out there on the internet and subjecting myself to potential judgment and criticism. But I knew focusing on my writing and helping others with my words was what I needed to feel fulfilled in my life, so I persevered. And I’m so glad I followed through in that because I’ve accomplished things I had never thought of doing, all because I launched this little blog of mine.

My biggest challenge this decade:

That’s a toss-up. It’s between the hardships I had at my first job and the break-ups I’ve had with friends over the decade.

A few months into my first job out of college at a global media agency in downtown Chicago, I was placed onto a new, under-staffed team and the hours started to get longer and longer as a result. I was learning a lot but I found myself working consistent 14-hour days and living a very unhealthy lifestyle. I remember coming home crying a lot and being frustrated that I ate all my meals at work and had no time for myself to spend time with friends, work out and do the other things I loved to do. It was a really dark time in my life, but it did teach me to never settle for less than what I deserve and to always speak up, despite what the consequences may be. I did everything in my power to instill changes within the team, going all the way up the chain to the Group Director and then walking into the HR office to address my concerns. Unfortunately, nothing changed, but that’s when I knew I deserved better and left the company.

I mentioned in my post about my shrinking friend circle that I’ve had friends come and go through the years, but some of those have included confusing and difficult “break-ups.” In the end, I know we’re better off not being in each others’ lives anymore, but at the times the break-ups were happening, the people pleaser in me desperately wanted to make amends and do everything in my power to fix the friendship. It was a challenge for me to hear negative words about me come out of my friends’ mouths or to be completely cut off with no explanation. I saw a quote on Pinterest the other day that really struck a chord with me though that stated:

“Stop chasing people. If they block you, cut off contact, ignore you…let them go. Let those who naturally gravitate to you enjoy your energy. We spend so much time begging for those who wouldn’t blink twice at the thought of you. Cherish those who are there by choice, and not there because you chased them every time they decided to escape.”

What I’ve accepted from these challenges with friendships is that:

  • We can’t control other people’s opinions – we can only control how we react (or don’t react) to them
  • The friends we keep aren’t always good for us so it’s often better we let them go
  • Some of the friends we make are only supposed to be in our lives for a short time

My favorite days of the decade:

Our wedding day (September 23, 2017) was undoubtedly my favorite day of the decade. Having all of Adam’s and my family and friends in one place was so special. It ended up being the hottest day of the year and broke a weather record (a whopping 95 degrees) and the A/C on our trolley blew out as a result 😂 so it was not only a day full of love, but also a lot of sweat and laughter.

Kelly and Adam in front of the Congress Hotel.

Our engagement day (November 1, 2015) was also a pivotal day of the decade. It was a beautiful, warm fall day in Chicago and Adam proposed at the Alfred Caldwell Lily Pond in Lincoln Park, with a photographer capturing the special moment! We happily called all of our closest family and friends afterward and went to a delicious Italian dinner downtown afterward.

The day Adam and I took a cruise through Milford Sound in New Zealand in November 2017 ended up being a favorite of mine because we were in such an untouched, pure part of the world and got to witness dolphins, seals and penguins in their natural habitat. Plus, any time I get the chance to get on a boat, I’m a very happy girl!

Kelly and Adam stand on a boat in Milford Sound.

Adam’s and my last day in Paris in May 2018 is one of my favorites days of the decade too. We walked up the hill in Montemarte and stumbled upon a square of different artists selling their work. We ended up purchasing a piece of art that now hangs in the living room of our condo which always brings back happy memories of that day. We ended that day on the Seine for a sunset river cruise. We watched the sun go down over the beautiful city of love and I truly felt like I was in a movie.

Adam and Kelly stand next to Pavlos, a Parisian artist.

Lastly, I had coordinated a 15-year reunion for my grade school class back in the summer of 2018.  I know, it sounds super weird – who does grade school reunions? But we were a tight knit group, since we went to a Catholic grade school and were together kindergarten through 8th grade and only had 56 people in our class. We all met at the local dive bar in our hometown and a lot of our parents showed up and we drank the night away. The priest who was at our church when we went to school even showed up! 😆 It was a hilarious blast of the past kind of night.

St. Gilbert alumni at Charlies in Grayslake, IL.

New habits I cultivated:

At the beginning of the decade, I was still in college and not treating my body in the right way. I was eating unhealthy foods and binge-drinking multiple days a week. I secretly hated drinking all the time but I didn’t want to be called “lame” or have FOMO, so instead, I conformed. And because of that and what I was putting into my body, I never felt 100% happy.

It really wasn’t until I left my first job after college that I was able to get both my physical and mental health on track. I discovered Classpass and developed an exercise routine particularly with barre and pilates, two workouts I now absolutely love. I learned the right foods for me to put in my body and focused on making more whole and clean meals at home. I went to therapy to work on my mental health and anxiety. Oh, and I stopped binge-drinking (for the most part anyhow 🙃). I’m so glad I’m ending the decade in a much healthier way!

The thing that scared me most:

A few years ago, I was asked to speak at Salesforce Chicago World Tour. Except, I wasn’t really asked, it was more like a “hey, we need a speaker so you’re going to do this.” It was only a few days before the conference and I had to memorize a talk track for a 45 minute session I’d be co-leading in front of over 200 Salesforce clients. I haven’t been that terrified in a long time and I remember having to really calm myself down moments before the session started, as I have social anxiety and public speaking is one of my biggest fears (something I’m working on). In the end, I powered through it and felt a surge of excitement afterward. I learned from that experience that doing the things that scare us is ultimately what is going to help us grow and feel accomplished.

My best purchase of the decade:

My condo in Chicago has been my best (and most expensive) purchase. Adam and I purchased it before turning 30 and we felt a sense of achievement from being able to do that. For four years prior to that, we lived in what felt like a shoebox while we saved money for our down payment. But in the end, it was worth it. While our first official home may be on the smaller side, it’s a home I can call my own in a neighborhood that I love.

My biggest career break-through moment:

Landing my job at Salesforce was a huge break-through for me professionally. Salesforce wasn’t even on my radar and it came about because I reached out to a previous contact I had met that had worked at another company I was interviewing at. As we got to talking over the phone, he mentioned that Salesforce too was hiring for a similar role. I interviewed and was told I got the job – but then Salesforce went on a hiring freeze for over three months. I waited it out, crossing my fingers that the role would open up again. After what seemed like forever, I ended up getting hired at a time when Salesforce was on the upswing and growing quickly. It’s been an honor to be a part of the growth these last 5 years and work for a company that was dubbed the #1 Place to Work in the World last year.

Kelly at Salesforce Connections 2018.

The biggest positive impact on my life this decade:

Hands down, my husband, Adam. He’s brought so much love to my life. He truly is my other half and my best friend. I feel incredibly lucky to have met him back in 2011 at Homecoming at our alma mater. How we never met in college still baffles us, considering we had so many mutual friends. But I believe everything happens for a reason and that was when we were meant to meet! We have created so many incredible memories together since then and I can only imagine what the next decade will bring.

Adam and Kelly on their wedding day.

Top things in my day to day that I loved:

  • Being outside, whether that’s sitting on my balcony with a book or writing in my journal, going for a walk, or sitting on a patio at a local Chicago restaurant during the summer
  • Working on everything Lipstick & Ink and getting back into my writing
  • Helping or teaching others, whether it be my clients with the Salesforce products they purchased, my contacts who need guidance when it comes to their careers or their resumes and cover letters, or my friends who want my opinion on something
  • Being able to set aside time for me to relax on the couch and watch TV
  • Hugging Adam and telling each other “I love you” any time he or I leave our home or before we go to bed

My favorite travels of the decade:

I didn’t travel a lot growing up, but I always had this inherent urge to see the world. I didn’t really get the opportunity to travel a lot until I started making my own money and putting it towards trips I wanted to take. This last decade, I’ve traveled more than I ever have and I’ve been to many placed I’ve always wanted to see. The two standouts are New Zealand (for Adam’s and my honeymoon) and Paris. We loved Paris so much that we are going again next spring!

Kelly and Adam stand in front of the Notre Dame in Paris, France.

Something I wish could have happened this decade:

My junior year of college, I begged my parents to let me study abroad. It seemed like I was the only one of my friends not getting the opportunity to go and I desperately wanted to have that experience. Unfortunately, the only way I was going to go was if I got their sign-off and because they were adamantly against it, I didn’t get the chance to study in Manchester, England (where I wanted to go). It still to this day remains the one thing I really wished I could have done.

What I wish I had done better:

I can get anxious and frustrated easily, especially when things are out of my control. This usually causes my patience level to dip and I find myself getting pretty snippy and short with people. I’ve let my emotions get the best of me over this last decade from time to time and I wish I could have controlled that part of me better. It’s a constant work in progress, but my hope is in 2020 and beyond that I can calm myself down more and always come from a place of kindness and patience.

What I overcame this decade:

The biggest thing I’ve overcome this decade has been the fear of judgment. It’s not to say that I magically don’t care what others think anymore because I truthfully still struggle it from time to time. But overall, I’ve pushed myself to do things this decade that I knew would maybe rub people the wrong way or lead me to be talked about behind my back but I’ve learned to stay authentic and true to myself and do my best to not pay attention to other people’s negative thoughts or feedback.

My biggest lessons of the decade:

I wrote last year’s reflection post about life lessons that I learned in 2018 and I’d say those six lessons I wrote about are my top lessons of the decade:

  • Hard work will always pay off
  • Continually push yourself out of your comfort zone
  • Focus on quality friendships and surround yourself with those who inspire you and motivate you to be better
  • Accept the things you cannot change
  • Remember to slow down and appreciate the journey and celebrate accomplishments (#IAmRemarkable)
  • Be unapologetically yourself and stay true to who you are

What I’m looking forward to doing in the next year:

I’m really looking forward to writing and finishing my first book in 2020. I’m also looking forward to heading to Africa to volunteer in February and immersing myself in a culture I’ve never been exposed to.

What I want to achieve in the next 10 years:

I want to:

  • continue volunteering, giving back and making an impact
  • publish my book & ultimately write more books
  • grow Lipstick & Ink – in whatever way that may be
  • continue growing my career at Salesforce
  • start a family

Kelly in Charleston, SC.

What I will stop, start, and continue in the next decade:

  • I will stop wasting so much time on social media and focusing more of my time on the things I actually want to do, such as write, read and exercise.
  • I will start going to bed earlier and getting up earlier to have more productive days (I need to banish my inner night owl)!
  • I will continue being authentic to who I am and following my passions, despite my self-doubt and fears.

I hope you have a happy and healthy new year and roaring ’20s decade ahead. It’s going to be a good one.

Pink lipstick stain

Welcome to Lipstick & Ink®, your home for everything career and life inspired. I’m Kelly, a Chicago-based career coach, branding consultant, and speaker.

Whether we’re working together on achieving your career aspirations, refreshing your professional documents, or crafting your brand, think of me as your career sidekick who is going to push you to your potential and cheer you on every step of the way.




  1. Very good Kelly! I enjoyed reading your post. I’ve never been to New Zealand or Paris and they both look amazing. Regarding Salesforce, I think I saw your company listed in the recent Chicago Tribune publication about the city and state’s best place to work. Sounds really awesome. You are so organized. Keep up the great work!


    • Thanks for reading and sharing your thoughts, Reid! NZ and Paris are incredible, I’d definitely add them both to your bucket list! Have a happy new year!!


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